Everytime
by Zeiskyte
Summary: And with the February breeze nipping at his skin, Leo leaned his head back against his back door to get a better look at the stars. - Leo, helplessly in love with his best friend's younger sister, can't sleep the night before Valentine's Day. A short drabble set in a modern AU.


Leo twisted and turned upon his bed for the umpteenth time that night. Pulling his covers on, kicking them off- it was an endless cycle that he was sure would never end. The hours passed by nevertheless, and he knew sleep would fail to claim him. The moonlight pouring in from his window was enough of an incentive to pull him to his feet to throw on a light jacket before heading out.

At nearly three in the morning and underdressed in the chilly night, Leo nearly ran right back into his house, but somehow, the bitterness of the cold seemed more welcoming than his abode. So he tugged his jacket closer around his chest and found himself sitting upon his back steps, goosebumps littering his skin.

The wind was light, barely whipping at his hair, and distantly, he wondered if anybody would notice his absence. Of course, it was the middle of the night and no one sane would be awake, so he pushed the notion aside. Time alone was time to think, and overthinking was one of Leo's favorite pastimes.

The sudden pang of being alone tugged at his heart. Never before had he cared about Valentine's Day, dismissing it as a silly holiday created to sell chocolates and stuffed animals to foolish love birds... but now, it seemed to be the sole thing running through his mind.

Leo could not pinpoint exactly when the sight of hair as pink as peaches and a tentative smile would start to make his heart race. Somewhere down the line of hanging out with Takumi in and out of school, he had developed a crush of his best friend's younger sister. He had yet to tell a soul, but knowing how nosy his siblings were, it would not be a surprise if they had already found out.

He shut his eyes, sighing to himself. Had he ever said a single _word_ to Sakura? Perhaps a mumbled greeting or goodbye when he accompanied her brother somewhere. Leo felt his heart sink at the thought. If they had not even shared a single conversation, it was unthinkable to muse _courting_ her. Especially not when his crush was his best friend's _younger sister_.

And with the February breeze nipping at his skin, Leo leaned his head back against his back door to get a better look at the stars.

Some were gathered together in a clump while others had a clear distance between them. How ironic it was that even the _gods_ were mocking him? He chuckled lightly, a smile tugging at his lips at how _stupid_ this all was.

Here he was, at three in the morning, underdressed and possibly freezing to death- pondering about his unrequited love for someone he had not even held a conversation with.

Leo almost regretted mocking people for their crushes. Teasing Xander about Charlotte, Takumi about Camilla... The realization that _you can't choose who you have a crush on_ hit him like a slap in the face. It was almost enough to drive him to an apology, but his pride would not allow it.

And why would someone as kind and forgiving like Sakura want someone as insufferable as him? A person who could never find it in himself to get past his ego and do something as simple as apologize? Perhaps Leo deserved being alone and the pain of watching couples express their love for one another. And maybe Sakura would find someone worthy of her and not some pining idiot such as himself.

Hell awaited him tomorrow, but at least he could call it his.

Staying out all night and freezing to death was starting to sound far more appealing but Leo was no stranger to consequences. Begrudgingly, he pushed himself to his feet and tugged at his jacket again. The cold was beginning to sting, but he had a feeling that sensation would not be ceasing any time soon. If he didn't want to be a walking popsicle tomorrow, it would be best to head inside, defrost, and salvage any second of sleep he could get. After all, he had to look somewhat presentable while he got his heart broken.

Taking one last glance at the night sky above him, he scowled.


End file.
